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Alabama train derailment

When family members are engaged in group sex with another family member and something happens (superficial or catastrophic) to bring it to an early or unexpected end.
We was all banging cousin Shirley out back at the family reunion when uncle Bubba's liquor still blew up and started an Alabama train derailment almost instantly.

Derailment

When you are railing your rib, cleopatra, bottom bitch, and wife of 14 years. And you slip into the wrong hole. This is called a derailment, and doesn't matter what hole.
Jim: fuck this feels good
Susan: oooooohhh ya harder harder
Jim: (slips into wrong hole)
Susan: ooooaaaahhhhhhhh

Jim: sorry babe I derailed
Susan: ok, next time I dont cause a derailment into me
Derailment by Cochieman 456 November 27, 2020

Holbrook Derailment 

When a woman is engaging in anal sex with multiple partners, and accidentally defecates on the still erect locomotive of the final man standing.
Bro 1 “Dude Buster’s mom was pulling trains last night. I got there late and went last. As I was pulling out she shits on my dick.”

Bro 2 “Damn dude, Buster’s mom gaves you a Holbrook Derailment.”

Holbrook Derailment 

When having anal sex with many partners, a woman shats on the rod of the last man standing.
Bro 1: Dude your mom was pulling trains again last night. I got there late and went last. As I was pulling out of the station she dropped a log on my schlong.

Bro 2: Dude moms gives you a Holbrook Derailment

Holbrook Derailment 

When a woman is having anal sex with multiple partners and she accidentally shats on the schlong of the last man standing.
Bro 1: Dude your mom was pulling trains again last night. Got there late had to be the caboose. As I was leaving the station she dropped a log on my iron horse.

Bro 2: Dude moms gives you a Holbrook Derailment.
It is said of the situation where a person has the bad luck to make contact with his testicles against an undefined surface or object, intentioned or not.
Given the nature of the word, it is more appropriate to design cases where the interaction is made with a moving object, for example, a ball.
Although it is extremely painful for the victim, it tends to be considerably funny to people who witness it.
Today in the baseball game the pitcher took a nutshot; the baseball hit him in the nuts.

Man, I just watched the funniest nutshot video ever.
Nutshot by Uberflaven March 1, 2009
Word of the Day on June 26, 2026